Potassium Carbonate → 5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1-(2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)pyrrolidine	HCID 56776833	—
Reactant	6-iodo-5-phenyl-3H-furo[2,3-d]pyrimidin-4-one	HCID 58603279	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one	HCID 58603280	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

Compound 11 (242 mg, 0.716 mmol), 1-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)pyrrolidine 25 [prepared by Specific Method A2] (500 mg, 1.58 mmol), K2CO3 (247 mg, 1.79 mmol), and Pd(dppf)2Cl2 (524 mg, 0.072 mmol) were combined in a pyrex tube. After purging with N2, DMF (7.3 mL) and H2O (1.45 mL) were added and the tube was sealed. The mixture was heated at 80° C. for 5 h. After cooling to RT, CH2Cl2 was added and the organic layers were washed with H2O, followed by brine. The organic layers were then dried over Na2SO4 and concentrated to a brown oil. Flash chromatography (SiO2, gradient eluent: 0-15% MeOH in CH2Cl2), followed by trituration with EtOAc and filtration afforded compound 26.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07776867B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-445d734ccabb4481bd78e1754dc526e3
Source note	uspto-grants-2010_08